16206-77-2

Basic information

• Product Name: (5alpha,6alpha,14alpha)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol
• CAS NO: 16206-77-2
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.3377
• Mol File: 16206-77-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 476.2°C at 760 mmHg
• Flash Point: 241.8°C
• Density: 1.44g/cm³
• Vapor Pressure: 7.06E-10mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: (5alpha,6alpha,14alpha)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (5alpha,6alpha,14alpha)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol(16206-77-2)
• EPA Substance Registry System: (5alpha,6alpha,14alpha)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol(16206-77-2)

Safety Data

• Hazardous Substances Data: 16206-77-2(Hazardous Substances Data)

Upstream product

• 76-57-3 codeine 
• 111009-97-3 7,8-didehydro-4,5α-epoxy-3-(2-ethoxycarbonyl-2-propyloxy)-17-methylmorphinan-6α-ol 
• 34332-29-1 7,8-didehydro-4,5α-epoxy-3-(2-hydroxymethyl-2-propyloxy)-17-methylmorphinan-6α-ol 

Downstream Products

• 561-27-3 morphine diacetate 
• 20290-09-9 morphine 3-glucuronide 
• 36418-22-1 4,5-epoxy-3-hydroxy-17-methyl-7,8-didehydro-5α,6α-morphinanyl 6-acetate hydrochloride 
• 6703-27-1 C₂₀H₂₃NO₄ 
• 52-28-8 codeine phosphate 
• 5140-28-3 3-acetylmorphine 

Relevant articles and documents

Method for catalyzing asymmetric synthesis of codeine and morphine

The invention discloses a method for synthesizing codeine and morphine. The method comprises the following steps: (I) taking 3-butyne-1-alcohol as a starting raw material to synthesize a compound 6: (shown in the description) (II) compound 6 firstly has intramolecular Michael addition reaction under the catalysis of a spirocyclic amine catalyst, and then acid is added to perform the dehydration cyclization reaction to obtain a chiral compound 7 with a hydrogenated dibenzofuran structure: (shown in the description) (III) the compound 7 has allylation, ozone oxidation, Foucault reaction, epoxidation, Wharton oxygen transfer reaction, debenzylation, Mitsunobu reaction, DMP oxidation, and the conversion by virtue of the reduction of sodium borohydride and Birch reduction to obtain the codeine(shown in the description). Under the action of boron tribromide, the methyl protecting group is removed from the codeine to obtain morphine. Compared with the existing synthesis method, the total synthesis method of the invention is simpler, and the catalytic asymmetric reaction has the advantages of high enantioselectivity, high yield and the like.